It seems extremely hard to be able to drag and drop files between two finder windows with a single move on the trackpad - as soon you reach the end of the trackpad you'll drop the files,… in the wrong place.

How can you solve the drag'n'drop problem without using a mouse and still be able to use gestures?

Click and Drag

Press the physical button, then drag. While the button is depressed, you can reposition your "dragging" finger without letting go of what you're dragging.

One-Finger Tap & Drag

With Dragging enabled, tap the trackpad twice and start dragging on the second tap (instead of lifting your finger from the trackpad). There is a short delay from when you lift your finger from the trackpad and when the drag actually ends, during which, you can reposition your finger on the trackpad to continue dragging. To end a drag immediately (without the delay) you can tap the trackpad again.

Three-Finger Drag

Tap the trackpad with three fingers and drag all three fingers. This has the same delay as the one-finger drag, so you can reposition your fingers and continue dragging. Again, a single tap will end the drag without the delay.

Drag Lock

Drag Lock works with both the "one-finger tap & drag" and the "three-finger drag". When enabled, the drag does not end after lifting your finger(s) from the trackpad. Rather you have to tap/click the trackpad to end the drag.

In Snow Leopard, the Dragging and Drag Lock settings are in System Preferences > Trackpad, but in Lion they were moved to System Preferences > Universal Access > Mouse & Trackpad > Trackpad Options.

With Dragging enabled, you may notice a delay when tapping compared to when it's disabled (at least in Lion).

Three-Finger Drag with Inertia

This is easily the most fun way to drag. This is like the three-finger drag, but instead of moving all three fingers, you only move one finger, keeping the other two in place on the trackpad. When you do this, you can use a flick gesture with the finger that's moving and whatever you're dragging will continue to move after you lift that finger, gradually slowing down. It works very much like scrolling with inertia. As long as you keep your other two fingers in place on the trackpad, you can lift your third finger without letting go of what you're dragging.

If you wanted to, you could actually keep one finger in place on the trackpad and use two fingers for dragging, but that's a bit awkward.

I turned on 3 fingers for dragging in the trackpad preferences. There also used to be an option on there called Click lock, where you would double click and drag and then the file would stay with the mouse until you clicked again. I can't seem to find that particular option anymore, but I know that if you enable the three finger dragging gesture that it's supported, so you just tap twice with three fingers on the file you want and then start dragging, and tap again when you want to drop the file.

Holding with your thumb and dragging kills the thumb after a while. You can enable double tap to select (versus clicking) and drag in preferences> accessibility under the mouse area in Yosemite. Then just tap lightly twice and drag with your finger. You might need to have tap to click enabled under the trackpad settings. That's the best way to do it if you're on your machine all day and prone to repetitive strain injury.

In a way dragging to the corner counts as a gesture, right? ;)
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gentmattMar 3 '12 at 11:51

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I don't understand what this has to do with the question: the OP is asking about dragging-and-dropping files, not about hot corners or trackpad gestures. :S
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Dan JMar 3 '12 at 20:17

@djacobson You're right, I over thought this. I made the false assumption that what @ matteo has said was already clear - and that the problem was using the drag and drop in combination with gestures. But that's not the case.
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gentmattMar 3 '12 at 20:52